29 Winchester Street

Toronto, ON M4X 1A6 ( Cabbagetown-South St. James Town)

Quick Facts

Type: Fourplex

Style: 3-Storey

Size: Sq Ft

Age: Years

Taxes: $ 12,354 ( 2026)

Updated: 2026-10-27 17:43:45

Description

The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto\'s most storied neighbourhoods. With over 4200+ sq ft of living space (each unit is over 1000+ sq. ft in size), 29 Winchester offers a spacious and gracious living environment, complimented with multiple walk-out balconies, large windows, private decks and terraces, all overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and ensuite laundry in each unit. Parking is accessed via a private rear laneway (4 parking spaces at present including 1 tandem space, and the possibility to expand up to 6 car parking on site). Highly desirable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.

Extras

Fourplex

Property

Status: For Sale

MLS #: C14111438

Price: $ 2,900,000

Address: 29 Winchester Street

Type:

Style: 3-Storey

Size: Sq Ft

Age: Years

Front On:

Taxes: $ 12,354

Tax Year: 2026

Lot Size:

Neighbourhood: Cabbagetown-South St. James Town

Nearest Intersection: Winchester & Parliament

City: Toronto

Postal Code: M4X 1A6

DOM: 15 Days

Last Update: 2026-10-27 17:43:45

 

Building

Interior

Bedrooms: 4

Bathrooms: 4

Rooms: 0

Kitchens: 4

Family Room:

Fireplace:

Basement: Apartment,

Central Vacuum:

 

Exterior

Exterior: Brick,

Driveway:

Garage: Lane Private

Garage Spaces:

Parking Spaces: 4.00

Pool:

 

Utilities

Electricity (Hydro):

Gas:

Phone:

Cable TV:

Heat Type: Baseboard

Heat Source: Electric

Air Conditioning: Wall Unit(s)

Water:

Sewers:

 

Features

 

Rooms